Preparation method of furosine
A technology of furoamic acid and protonic acid, which is applied in the production of organic chemistry and bulk chemicals, can solve the problem of few synthesis routes, and achieve the effect of easy availability of raw materials and low cost
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Embodiment 1
[0025] like figure 1 As shown, the present embodiment provides a method for preparing furoline, comprising the following steps:
[0026]
[0027] Step 1: stirring compound 1, compound 2 and palladium-carbon in a mixed solution of an organic solvent and an additive under a hydrogen environment, after the reaction is complete, filter out solid impurities, concentrate and purify the solution to obtain compound 3;
[0028] Step 2: adding compound 3 and protonic acid to an appropriate amount of solvent to react, removing the amino protecting group, after the reaction is complete, adding an inorganic base solution, adjusting the pH value until a solid is precipitated to obtain furoline or its salt.
[0029] In the above step 1, the additive is a pure solution or an aqueous solution of hydrochloric acid, sulfuric acid, citric acid or acetic acid. The molar ratio of compound 1 to the additive is 1:1 to 100:1, preferably 10:1.
[0030] The molar ratio of compound 1 to compound 2 i...
Embodiment 2
[0036] 1.24g compound 1, 2.46g compound 2, 30ml tetrahydrofuran, 60 microliters of acetic acid, 200 mg of palladium carbon (palladium loading 5%) were added to 100 milliliters of single-neck round-bottomed flasks, and the round-bottomed flask was replaced with hydrogen after stirring, After stirring at room temperature for 27 hours, the solid was removed by filtration, the solution was concentrated, and purified by column chromatography (ethyl acetate / n-hexane=2:1) to obtain 1.9 g of yellow gummy semisolid, which was compound 3 (yield 54%).
Embodiment 3
[0038] 1.1 g of compound 3 and 15 ml of hydrochloric acid (2N normality) were added to a 100-ml round-bottomed flask, and the mixture was stirred at room temperature for 18 hours. Then, aqueous NaOH solution (2N equivalent) was slowly added to precipitate a white to yellow flocculent solid, which was filtered and dried to obtain 618 mg of compound 4 (yield 78%).
[0039] To sum up, the present invention adopts 2-(furan-2-yl)-2-oxoacetaldehyde raw material to synthesize furosine, and this raw material is a known compound, which can be purchased in the commercial market or obtained according to the published technical document Tetrahedron Letters, 58(7), 658-662; 2017 was synthesized and obtained, so the raw materials are readily available and low in cost, and are suitable for industrial production.
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